Sweat was just starting to cool on my body. Juliette’s breathing was slowing from the tit-heaving panting she’d been engaged in moments ago. We’d just fucked like gangbusters, and I was basking in the afterglow when Juliette surprisingly said, “I bet I could be a man.”
Not what I expected to hear from my girlfriend after sex.
“Yeah?” I replied with a chuckle.
“I mean it.” She propped herself up on one elbow. “I’ve done makeup, costuming. Put me in a group of people who don’t know me, with a boyfriend on my arm, and I could make them think I’m a gay guy.”
“Why do you need to be gay?” I asked.
“I could pull it off better, I think. What do you say, Scott? Wanna be my boyfriend?”
“I’m already your boyfriend.”
“Then, how about if I was your boyfriend?”
Although I was a little startled by her proposal, it wasn’t entirely out of character for Juliette. She latched onto enthusiasms easily. For example, since we’d been together, she’d tried waterskiing for the first time — just one day deciding she would do it and following through within a week. Her adventurous nature had benefitted me, too. She was fun in bed, not leery of getting wild.
“Well?” she prodded.
I shrugged and said, “I’ll play along, if you want. Do I have to act differently toward you if you’re my boyfriend?”
“Just be your usual self. And I’ll be the best piece of man-ass you’ve ever had.”
“Since I’ve never had man-ass, that’ll be easy.”
But Juliette’s eagerness was infectious, and I was intrigued by the notion. How would people perceive me if they thought I was gay? It sounded like fun.
My girl had indeed done professional stage makeup and costumes. She threw herself into her latest work, while I tried to scrounge up a venue for her gender-bending debut. My friends knew I was 100 percent straight, so my usual haunts were out. Fortunately, we lived somewhere with lots of options. I found something I thought was suitable on the internet and suggested it to Juliette.
“It’s a gallery showing,” I said. “Look, they’ve got photos of some of the art. It’s pretty cool, and it’s definitely a place we’ve never been to before.”
“Perfect!” she said, clapping her hands.
She’d been rooting around in my closet and combing thrift stores for outfits. She already had a plan for the makeup part, but she hadn’t showed me anything yet. It would be better as a surprise, she told me.
Finally the night came, and she emerged from the bathroom after some lengthy preparation.
My jaw dropped. I’d expected something sensational, but she seriously shocked me.
“Jesus!” I shouted. “Dude, you look great!”
And yes, that “dude” just slipped out. Because my lovely sexy girlfriend now looked like a guy. She was wearing one of my shirts, and she must have strapped down her breasts. Her pants were baggy, and she wore thick-soled shoes. Her hair was hidden under a cap, but enough of it stuck out to cover the sides of her face to just under her earlobes. She didn’t quite have a five-o’clock shadow, but her makeup tones insinuated it.
That wasn’t all of it, though. Her mannerisms also added to the illusion. She walked up and down the room, and goddamn if she didn’t move with a masculine gait. I’d maybe never been quite so aware of how differently men and women carry themselves — until I saw my girlfriend shift gears.
She half strutted, half loped. She slung her hands in her pants pockets. Her shoulders were high, but there was a cocky looseness to her walk.
“What do you think?” she finally asked, even though I’d already expressed my opinion.
I wanted to reassure her, so I replied, “I think I’ll have the sexiest boyfriend at the show.”
We went downtown. She’d changed how she spoke, too, keeping her voice to a lower register. We entered the gallery. It was a good turnout. Not a hoity-toity crowd, just a bunch of people who appreciated art.
The pieces were interesting. We mingled, and I played my part. I introduced Juliette as Julien, and everybody appeared to accept “him” as my escort. Some gay folks were there, too, but nobody looked at us sideways. I put my arm around Julien’s shoulders.
Unexpectedly, some part of me was strangely turned on by our role-playing. Juliette really did make for a pretty man, and identifying as half of a gay couple was a lot easier than I would’ve suspected.
Julien really was the hottest guy there. And “he” was all mine!
When Juliette was satisfied with her performance, we ducked out. Heading back to my place, we laughed triumphantly. Our evening had been a success, and now our excitement levels were soaring into the red.
We hurried up to my apartment. She went in ahead of me, and I heard her unbuckling her belt. When I entered close behind her, I saw she’d pushed her pants halfway down and was shoving her lovely bare ass in my direction.
“I promised you ass. Here it is. Fuck it!”
My cock practically tore its way out of my own pants. Desire lit me up. I’d done anal with Juliette before, and it was always intense. That night the idea felt even more charged. She didn’t remove any more of her clothing, and the masculine look persisted.
She stood gripping the back of the couch and thrusting her naked ass my way. I got out of my clothes, letting my cock spring free, and moved in closer to her exposed rear.
When I was near, she looked over her shoulder and demanded, “Put that cock in your boyfriend’s asshole!”
I hesitated, but her comment made my balls tingle. Silence stretched out, and she glanced at me again. I could tell she was about to call it quits with the role-playing if she sensed I was uncomfortable.
But all at once I said, “You bet I’m going to fuck your tight ass, dude.”
I saw her straighten and heard the gasp of indrawn breath. Indications of her excitement. She wanted this, and I didn’t want to disappoint her.
I stepped in behind her. A pearl of milky pre-come had gathered on my cockhead. I swiped it off and rubbed it between my thumb and finger, then I dipped my hand between the halves of her ass and grazed her waiting pucker.
She groaned, still keeping her voice in that low, mannish register, and said, “Yeah, you’re making my cock so hard!”
I was unsure why I found that so exciting. Maybe it was just the kink of the whole scene, even though anal sex was nothing new between us. But this was what Juliette could do: Make things new, and wild, and fun.
That night, apparently, it was going to be manly fun.
I smeared my copious pre-come over her hole, and she ground back against my touch. Her hips rocked, and her shoulders rolled, but she was still mostly dressed. It wasn’t easy to tell it was a woman under those baggy clothes.
“I love it when you finger my hole,” she said.
I snaked my finger into her, wriggling it the way I knew she liked. Her asshole was tight around my digit, and my cock twitched in anticipation. I moved in right behind her, withdrawing my fingertip and rubbing my thick cockhead along the groove of her ass halves.
I was tingling all over, and my bare skin felt charged with electricity where it brushed against the fabric of her clothing. Only her lovely ass was exposed.
I rubbed some spit onto my knob, then set it to her asshole. Anal sex, I knew, required a gentler touch than regular fucking. I pressed forward slowly, gazing at the ring of her hole gradually expanding and finally swallowing my plum-sized cockhead.
She thrashed, still gripping the back of the couch. Her hair remained under the cap she’d worn that night. The illusion she had carried off was still in effect.
“Oh, your cock’s bigger than mine!” she gasped.
Obviously the gender-swap game hadn’t ended for her. I should be a good sport about it, I realized.
“That’s why I’m fucking you in the ass,” I said. “The bigger cock always wins.”
I felt a shudder go through her and knew electrical excitement was coursing inside her. She got that way when something especially turned her on.
With a little more forward pressure, I eased another inch, then another, into her backdoor. Her back channel clenched me, and my hands cupped the swells of her ass.
“Give it to me like a man!” she demanded, pushing her ass back toward me in encouragement.
At that, I knew she was ready for all of me. I slotted myself the rest of the way in, savoring the slightly alien angle, and buried my cock in her ass.
We stood like that, connected so intimately. I had always enjoyed the trust and vulnerability that went with butt-fucking. Juliette also took extreme pleasure from it. I’d made her come that way before, and I certainly wanted to do so that night.
When I started stroking in and out of her, I added a running commentary. I would continue to role-play, if that was what she liked.
I fucked my girlfriend’s ass with mounting gusto. She responded with cries of her own, going on about her “cock” and how she liked having another guy fuck her.
My fingers sank into the flesh of her ass. I was slamming into her from behind, knees bent and nearly up on my toes. My balls smacked her body, making hollow thwacking sounds. I drove deep into her with every thrust, and she took every bit of my cock with enthusiasm. She shrieked with delight, and a new violent shudder started in her. I felt it climb her body and knew she was in the throes of a major climax.
I hurried to join her and pounded her ass energetically. She let out a howl, and as she shook with orgasmic fury, the cap flew off her head and her hair spilled around her shoulders. Her pants dropped the rest of the way down her legs, revealing her lithe figure.
With an impulsive yank, I tore my shirt off her and came with convulsive jets in her ass. She was a woman again, and I jizzed hard inside her.